AI Article Synopsis
- A new method for creating chiral dioxa-caged compounds from levoglucosenone is introduced, using a 3-step cationic cyclization process.
- High yields and selectivities were achieved with the help of Montmorillonite K-10 as a catalyst.
- The research also explores K-10's effectiveness in rearrangements to produce pyran-3-ones, revealing notable reactivity differences in similar alcohols, which were analyzed using DFT calculations.
Article Abstract
A short and efficient methodology for the synthesis of chiral dioxa-caged compounds from levoglucosenone, a biomass-derived enone, is herein presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.
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| http://dx.doi.org/10.1016/j.carres.2014.07.019 | DOI Listing |
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